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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Relaxing 2 Room Suite with Private Bath/Deck/Patio
Entire guest suite · 3 guests · 2 beds · 1 bath
Relaxing 2 Room Suite with Private Bath/Deck/PatioWelcome to this spacious, quiet and relaxing furnished suite (private entrance with own deck and patio/fire pit). It is truly in an amazing location; walking distance to Burlington Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking in the driveway. Our place is good for professionals, responsible students, couples, solo, business travelers, families (with kids).
room in beautiful home and garden
Private room · 2 guests · 1 bed · 1.5 shared baths
room in beautiful home and gardenThe house is a cape, on a tree lined street with new kitchen and bathrooms. It is well maintained, clean, peaceful, newly painted and furnished with a blend of antique and contemporary furniture.
Relaxing and Comfortable Home Away From Home
SUPERHOST
Entire guest suite · 4 guests · 1 bed · 1 bath
Relaxing and Comfortable Home Away From HomePrivacy and comfort in complete lower level of this home. Private entrance and no shared space all within 5 minutes of shopping/restaurants and major highways. The space features a large kitchen w/dining area for 4pp, 1 bedroom with queen sized bed , living room with 65 inch tv with full cable. 1 full Bathroom with shower and tub. Washer and dryer are also included. Professionally maintained and enclosed backyard and patio area for outdoor seating. King Koil air mattress in bonus room.

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Popular amenities for Winchester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winchester

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Guest Suite w Free Parking - 12min Train to Boston
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Couples Retreat - Charming Colonial Home
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Warm home in Lexington, walk to town, nature trail
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Studio / across from West Medford commuter rail
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Renovated—Beautiful—Clean—2BR—Parking—Washer|Dryer
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Lovely 2 bedrooms in two family House
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Newly Renovated | Private Suite - Free Parking
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Unique Loft/ Studio Guesthouse (super convenient)
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3 Beautiful Victorian house
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Artsy Guest Suite close to Harvard & Tufts!
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Lovely independent in-law suite with free parking
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Private room in our spacious and welcoming home